Ballad of Shillelagh O'Toole: Lyrics, Video, Back Story & Merch

Styled after the classic sea songs of yesteryear, here's a salt-flavored ballad about an old orange-haired pirate who's proud of his big "shillelagh", who abuses women, who wreaks havoc among travelers from many nations, and who sinks perfectly sound ships for fun and profit, aided and abetted by a corrupt and soulless crew. (If you want to go reading other things into that – well, that's your business!)

The twisted marauder, Ireland's cruelest pirate, wreaks blackthorn havoc upon the high seas until one fateful day when he meets a man whose shillelagh is bigger than his. Herein lies a Karmic life lesson to which certain People in High Places these days would do well to pay heed.

The lyrics below are only slightly tweaked from an original draft I "penned" on my tablet between 04:30 and 06:00 one eastbound jet-lagged morning after a night of evil dreams in the fateful autumn of 2016. Out of the mass of lemons coursing through my fevered brain I managed to make a bit of lemonade, after which I felt enough better that I was able to snatch a couple more hours' sleep. All hail Saint Patrick! Full speed ahead!

Original Song Lyrics

Shillelagh O'Toole was an old Irish pirateHis ship roved the oceans afarHis raiment was green as the meadows of ÉireHis heart black as fresh Stockholm tar

CHORUS:Nor cutlass nor dagger e'er would he carryNo pistol did ever he bearJust had him a big old blackthorn shillelaghLead-filled, with some nailsDriven in here and thereOh never was any pirate more cruelThan the old Irish pirate, Shillelagh O'Toole!

Shillelagh O'Toole were a merchantman's curseOut o' fog banks his vessel would pounceHis crew they would board, wielding pistol and swordWhile O'Toole swung that stick's every ounce

Shillelagh O'Toole he'd no mercy at allHe sank brigantines, schooners, and barquesOn their captains' heads his blackthorn did fallAnd he tossed each dead corpse to the sharks

CHORUS

Shillelagh O'Toole had a shriveled-up soulAs knotty and black as his stickWhether man or woman, young lad or maidenHe bashed all their heads in right quick

Shillelagh O'Toole's beard it was redHe'd blood on his hands, and a price on his headHis black cudgel cut many a sailor's life shortThey chafed for to hang him in many a port

CHORUS

Shillelagh O'Toole at last met his matchWhen he boarded the Maid O' CadizThere he encountered young Davey O'DowdWhose shillelagh was bigger than his!

Shillelagh O'Toole and Davey O'DowdFought like demons, so the tale does tellBut hardy young Davey had the bigger shillelaghAnd he knocked old O'Toole straight into Hell!

CHORUS

Davey O'Dowd was hailed as a heroFor the Maid O' Cadiz he did saveHis legend lived on in story and songLong after he'd gone to his grave